Please Help! a dating mommy dilemma

Last week I had drinks with an old (sorry – longtime) friend of mine who is a fellow dating mommy.  My objectives for the evening were (a) get to the bottom of why she’s been acting so crazy, and (b) recruit her to be part of the dating mommies blog.

I accomplished objective (a).  (b) she informs me, will never happen, but she was left less than satisfied with my advice/opinions on (a), so she agreed to let me get more perspectives from our readers.

This is where you come in…..she wants advice, and I don’t seem to cut it for her (I think she just didn’t like my answer HA!)    Would you be willing to help an old friend?

The background:

A few weeks ago, she was introduced to a friend of a friend.  They hit it off instantly online.  They have great conversation, a strong sense of openness in communication, a great ability to share perspectives, life stories, etc.  Pictures were exchanged, and there’s definitely chemistry via photos.   Phone conversations initiated, and again, great communication chemistry, and she says “he’s got a HOT voice”.

About her:

She’s 42 years old.  She’s been married once & divorced almost 5 years ago, and has 3 kids.  She is the primary parent.  Since her oldest child was born, she has been financially supporting the family.  She’s my best friend because she is full of compassion, wisdom and optimism.  She sees the best in everyone.

About him:

He’s 39 years old.  He’s never been married, has no kids.   He seems to love kids and seems to be completely head over heels for her.   He is currently living with his father, who recently lost his wife.  He does not currently have a job.  He’s very
attentive, and, like she said, “he’s got a HOT voice”.

The dilemma:

Is the living with his father and/or the lack of current employment a deal breaker?  Let’s hear what you dating mommies out there have to say…..

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4 thoughts on “Please Help! a dating mommy dilemma

  1. Ok, as a dating daddy, this screams “red flag” for me. 39, unemployed and living with Dad? Having said that, I’d want to know more before recommending a toss to the curb. E.g. When was he last employed/What was his longest relationship/Was he ever engaged? But the simple fact is that I’ve heard too many horror stories from other dating mommies (and even singles in their late 30’S) where just this type of guy ended up being gay, bi, psycho or a serial dater. My two cents.

  2. There are a lot of nuances here for me.

    1) What kind of relationship is she looking for? Something that makes her feel good, happy, desired, light? Then who cares. He may not be Mr. Right, but he may be Mr. Right Now, like a reset button for the soul. Sounds like she has her hands full right now anyway, so maybe all she needs is a little light distraction without the pressure of a relationship. (As a bonus, entering into it with no expectations may actually make discovery easier, and there may be something there after all, like the “wife” she wants to take care of her homestead…?)

    2) Living with extended family actually kind of turns me on. For a lot of reasons. We are the only country in the world with this bizarre obsession of moving out and going solo. It is a ridiculous waste of resources, not to mention draining us of time and energy that we could share the burden with instead. Cross-generational living also has been proven to lessen depression, increase compassion and ground us. I’m a fan.

    For a guy to be able / willing to do that in this day and age shows an ability to make a rational decision in hard times, rather than the reverse, which is a damned sexy quality in a partner.

    A guy who has a good relationship with his parents is WAY better than one who has a chip on his shoulder, any day. I’ve been with plenty of highly successful men who were bearing huge grudges against their parents that were fucking up all of their relationships, they just couldn’t see it and deal with it. So no, this is not a deal breaker for me, at all.

    3) Unemployed? Join the club. Worst economy since the Great Depression…. What is he doing with his time? How’s his attitude? Does he have dreams and goals anyway?

    4) Never been married? Has he had serious long-term relationships? If no, THAT’S the red flag? If yes, then maybe not. Talk about the relationships he’s had and see what he’s learned about himself.

    At the end of the day, I always advise looking at this moment and asking yourself if THIS makes you happy, NOW. The ability to chose happiness now is one of the greatest struggles I see in women our age. We worry about all the “what-ifs” and forget that we can’t control those, we can’t predict the future, and we can’t change the world around us. If it makes you happy, now, then you should do it.

    You should do it rationally, safely and with both an open mind and clear boundaries. But don’t bring baggage and judgement into any new relationship. Even if he’s a billionaire widower who loves his kids and parents, your baggage will kill it. Leave it at the end of the last journey so you can start the new one fresh.

  3. I am with you on the daddy and unemployment part. The best is to ask questions, communicate with the guy instead of making assumptions.

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